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While Tamarindo in Costa Rica is no longer a sleepy beach town known only to a lucky few, we can still settle ourselves onto the sand and feel like we have the vast skyline to ourselves. Staying in Playa Langosta, the beach just south of Tamarindo, provides a welcoming relief from clusters of tourists while keeping us close enough for sunsets like this! Extra bonus: Have a friend or loved one in one hand and a cocktail in the other.

The water is usually calm and a bit warmer on the Nantucket Sound side of the island. Steps Beach is off Cliff Road about four miles from town, sandwiched between Dionis and Jetties, and is not on most people’s radar. Before you take on the massive set of stairs leading down, enjoy the view of Great Point Light off to the right. Steps Beach offers protected shores with gentle waves washing onto the sandy beach, and gray-shingled mansions dotting the surrounding sand dunes. Come prepared, as there are no lifeguards or facilities, and make sure to save some energy to make the climb back up the steps.

The supper club is reinvented for the next generation at Yvonne’s, banishing any possible ghosts from the former Locke-Ober’s, and leaving just enough of the old girl (the beautiful hand-carved original bar and woodwork) to recognize her former self. The entrance is a bit mysterious, and the outer-bar area a happening scene. Walk through the “library,” a cozy space that looks like it’s right out of an Anthropologie catalog, and you’ll find lime-green banquettes, fancy chandeliers, and a modern web of lighting. The small plates are meant for sharing and make it possible to taste a good many flavors from the kitchen. Baked oysters Savannah are a nod to the well-heeled crowd, combining lobster, porcini cream, and Parmesan into a decadently rich mouthful. Seared halloumi has just the right sweet-and-savory combination and is a favorite that doesn’t disappoint. Be sure to make a reservation; there is usually a line. Try one of their crowd-pleasing punch bowls presented in unusual vessels. The “Goodbye, Me"—with Moroccan-mint-infused gin, sake, watermelon, lemon, and champagne—lives up to its name.

One of Cancún’s oldest restaurants, La Habichuela was a 1970s original whose owner wanted a place to hang out with friends. It’s become an upscale dining room featuring local Mayan recipes alongside Mexican-Caribbean fare. The now iconic restaurant borders downtown’s Las Palapas Park, and has a charming backyard garden adorned with twinkly lights and climbing vines. Start the evening with balché, an ancestral Mayan drink made from the bark and roots of the balché tree that have been soaked in honey and water. For your entrée, try the amaranth fish bathed in flavorful tamarind and mango vinaigrettes.

Sustainability is the name of the game at h2hotel in downtown Healdsburg. The building is certified LEED Gold by the U.S. Green Building Council and has a living roof of grass and succulents that filters rainwater to reduce the impact on Healdsburg’s storm-drain system and neighboring Foss Creek. Inside the 36 rooms, sensors turn off lights, fans, and air conditioners when guests leave, and the bamboo flooring is layered with fair-trade, chemical-free rugs. Even the way the hotel approaches in-room beverages is green; instead of plastic water bottles, guests are given recycled glass wine bottles to refill at water stations around the property (there’s at least one on each floor). The hotel isn’t only eco-friendly; it’s swanky, too. Out back, along Foss Creek, a lap pool is an inviting spot to spend a hot and sunny afternoon. In the lobby, the bar at Spoonbar! Restaurant still turns out some of the tastiest craft cocktails in town. All overnight stays include complimentary breakfast and access to the hotel’s collection of Public bikes. There’s also a free yoga class for guests every Sunday morning. Be sure to see the on-site Hand Fan Museum, a passion project for Pam Sher, the matriarch of the family in charge. Also make time for a meal at Oaxacan restaurant Mateo’s Cocina Latina across the street (chef Mateo Granados is married to the owner of the hotel).

Let the Urubamba River set your course during a thrilling rafting adventure along the Ollantaytambo rapids, available through the Belmond. The river helped form what is now the Sacred Valley, and along the way you’ll not only sense its power, but also get a feel for some less visited corners of the region it created. You’ll pass towering eucalyptus trees and the ruins of Inca terraces and more as you make your way down river, ending with a picnic lunch before returning to the hotel by car. Photo by Rod Waddington/Flickr.

There aren’t too many opportunities in the Caribbean to ride on horseback to a cave. In Los Haitises National Park, located three hours west of the resorts of Punta Cana, Fun Fun (pronounced “Foon Foon”) Cave is officially known as the largest cave in the Caribbean. Though the cave itself is in the National Park, access to the land goes across a private ranch and requires a guided tour. While the nearly three-hour drive from the resorts of Punta Cana is a lengthy, bumpy, journey into the interior, the scenes from the window provide an authentic glimpse into rural Dominican life. Sugar cane sways, schoolchildren wave, and mangoes drip from the trees. Upon reaching the ranch where you begin the tour you are shimmied into a jumpsuit and saddled onto your horse. A 45-minute ride through the shaded forest brings you to the edge of the National Park. From here it’s another 30 minute walk through sun-swallowing trees until you reach the entrance of Fun Fun Cave. Sliding into a harness and climbing gear, entering the cave requires a 50 ft. repel into a tiny hole which can barely fit your shoulders. Once at the bottom, it’s a one hour slog through the depths of the darkness before reaching the other exit. Inside the cave, stalactites and stalagmites pepper the areas which fall in the beam of your flashlight, and at some areas you are forced to swim through the soothing, subterranean waters. Here, a lone rope helps guide visitors through the hidden recesses of the cave.

This tiny island is north of Isla Mujeres and Cancun and is only 26 miles long and offers visitors in search of a “Robinson Crusoe” experience the perfect escape. Long, sweeping beaches beckon with water sports, snorkeling, sport fishing, and total R&R. A shallow lagoon gives sanctuary to thousands of flamingos, pelicans and other exotic birds and creatures, allowing visitors the perfect spot in which to commune with nature. Several good restaurants and hotels are available and tours to area attractions can be arranged by ferry and small plane. Getting around the island is via bicycle or golf cart.

Named after an artistic city in central Mexico, Sedona’s Tlaquepaque Arts and Crafts Village is one of the best outdoor shopping spots in Arizona. Sycamore-shaded fountain-filled courtyards and vine-covered colonnades are home to over forty galleries, boutiques, and restaurants. (The architecture may only be a few decades old, but this is one of the most well-done ‘pseudo-Mexico villages’ in the U.S.) The emphasis is on Southwest sculpture, blown-glass, painting, ceramics, textiles, and jewelry. If you want to take a break from your red-rock ramblings, this is the place.

Housed in a former 1929 Nabisco box printing factory, the museum, which opened in 2003, is a must see for contemporary art buffs. Encompassing over 240,000 square feet, it showcases the Dia Art Foundation’s collection of Minimalist, Conceptual, and Post-Minimalist large-scale works from the 1960’s to the present. As you navigate through the exhibits, you’ll notice most of them are illuminated by natural light, courtesy of the building’s original skylights. Highlights include Andy Warhol’s shadow paintings; Louise Bourgeois’ imposing “Spiderwoman” sculpture; Richard Serra’s “Torqued Eclipse,” a series of vast circular metal sculptures; and Dan Flavin’s florescent light works.

Located in the former warehouse of the American Syrup & Preserving Company, Bastion offers customers a different experience depending on where they perch. On the bar side of the operation, one feels like a guest in the spacious digs of an artist, with mismatched furniture and lights strung from the rafters. Settle in and order craft cocktails and a platter of nachos gussied up with smoked meats. Or head to the other side, around the bar wall, where the staff prepares dinner in a warm, unpretentious space with chef Josh Habiger himself occasionally emerging from the kitchen to change the vinyl records. In lieu of menus, guests are handed bingolike cards with minimal descriptions (Monkfish Liver + Salsify or Black Sea Bass + Black Tea) and mark their choices there, placing their trust in the hands of Habiger and team cooking from an open kitchen.

The setting of Felina Bar feels somewhat like hanging out at a friend’s apartment: all vintage chairs and couches, with low lighting and jazz setting the scene. Don’t rush the bartenders, who mix drinks with great attention and will happily tell you about spirits and the burgeoning Mexico City cocktail scene.

Opened in 2011, Reykjavík’s Harpa Concert Hall and Conference Centre is not only the most significant classical music venue in Iceland (home to the Iceland Symphony Orchestra and the Icelandic Opera), but also one of the country’s most striking examples of modern architecture. Located close to the old harbor, the building was part of a larger development meant to breathe life into the downtown district (the plan was abandoned due to the subsequent economic crash, but funds to complete Harpa were found). The coruscating, eye-catching facade was designed by Icelandic-Danish artist Olafur Eliasson, and the spacious interior has four handsome halls, the largest of which can accommodate up to 1,800 seated guests. There are also smaller conference rooms dotted throughout the building, and the ground floor hosts a record shop, café and restaurant, and other public areas. In addition to classical concerts, the venue holds music festivals, pop shows, art exhibitions, and more.

The longest lines in the city form every day at Café Medina, a haven of Mediterranean-inspired breakfast, lunch, and weekend brunch dishes in the Library District. The decor here feels like a minimalist version of 1920s Paris, with aged walls, mismatched light fixtures, and a mosaic entranceway. Equally charming, the eclectic bistro fare ranges from pistachio-rosewater Belgian waffles to halloumi couscous and a harissa burger, spiked with preserved lemon and tucked into a pita with baba ghanoush and two fried eggs. Don’t miss the blistered flatbread, ideally paired with the honey-black-pepper mascarpone side. And finish with a lavender latte, a house-made turmeric soda, or a superb craft cocktail. If you don’t want to wait, skirt the crowds by visiting Tuesdays or Wednesdays for lunch, or arriving at 2 p.m. (an hour before last call).

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.